CN1925753B - Confections containing a blend of physilogical cooling agents - Google Patents

Abstract

A method for producing a confection such as chewing gum, as well as the confection so produced, incorporates a blend of physiological cooling agents, including menthyl glutarate and one or more of L-isopulegol and p-menthane-3,8-diol. In another embodiment the blend of physiological cooling agents is made in a modified release structure. The modified release/cooling agents combination is preferably obtained by physically modifying the properties of the combination of cooling agents by coating and drying. When incorporated into gum, these particles are adapted to enhance the shelf stability of the flavor and/or produce a modified release when the gum is chewed. In another embodiment, the blend of physiological cooling agent is included in a confection coating.

Description

Confectionery Containing Physiological Refreshing Blends

References to earlier filed applications

This application claims priority to US Provisional Application 60/548,471, filed February 26, 2004, under U.S.C. § 119(e); incorporated herein by reference in its entirety. the

Background technique

The present invention relates to confectionery, particularly chewing gum compositions, and methods of producing chewing gum and other confectionary products. In particular, the present invention relates to the production of chewing gum and other confectionery containing a mixture of physiological cooling agents. The physiological cooling agents can be treated to control their release and enhance their storage stability stability. Likewise, the physiological cooling agent mixture may be added alone or as part of a cooling flavor composition and used in a confectionery coating. the

There are several compounds known to have activities known as "cooling" and are referred to in the art as "physiological cooling agents". Physiological cooling agents may be perceived as cooling or refreshing when in contact with the human body, and especially the mucous membranes of the mouth, nose and throat. the

Numerous efforts have been made to perfect the use of physiological cooling agents in chewing gum and other confectionary formulations to enhance flavor compositions and control their release to enhance the taste of the chewing gum or other confectionery. the

U.S. Patent 6,627,233 (hereby incorporated by reference in its entirety) discloses various physiological cooling agents and combinations of physiological cooling agents including N-2,3-trimethyl-2-isopropylbutanamide (known as WS-23), and its application in chewing gum. The physiological cooling agents may be treated to modify their release from the chewing gum and may also be used in chewing gum coatings. the

Peppermint oil is currently used in oral preparations such as toothpaste, mouthwash, confectionery, including chewing gum and candy, and other food products for a "refreshing" sensation. Peppermint oil generally contains about 45% l-menthol, about 20% menthone, about 5% menthyl acetate, about 5% eucalyptol and many other ingredients. Peppermint oil can even be used in non-mint preparations, such as spearmint or oil of wintergreen flavored preparations, to induce this desired cooling effect. Consequently, peppermint oil was also subsequently found in the resulting non-menthol flavored preparations. the

1-Menthol is also known for its physiological cooling effect on the skin and oral mucosa. As the main component of peppermint oil, 1-menthol is widely used in food, beverage, dentrifice, mouthwash, cosmetics, lotion and so on. However, the disadvantage of using 1-menthol is its strong minty taste and the unpleasant smell that occurs in compositions with 1-menthol. the

Therefore, there is an urgent need to find a cooling flavor composition that contributes to a product with a long-lasting cooling sensation without undesired offensive taste or odor characteristics in the product resulting from the added 1-menthol . the

It would be desirable to provide a chewing gum or other confection that has a strong flavoring effect and does not exhibit the off-taste commonly associated with certain confectioneries, especially chewing gum. It would be desirable to provide a clean, high quality tasting confectionery with a good cooling effect. the

The invention also relates to coated confectionery, such as chewing gum. Chewing gum and other confectionery are usually coated with a hard or soft coating. The coating gives the manufacturer the opportunity to modify the taste, appearance, mouthfeel and nutritional value of the confection. the

For example, some consumers prefer an instant burst of intense flavor rather than the slow, mild release of flavor typically associated with confectionary products such as chewing gum. In order to provide a pleasing taste effect, manufacturers add various flavoring agents to the coating of the coated product. These flavors include spearmint flavors, peppermint flavors, wintergreen flavors, and fruit flavors. In addition to this, particularly strong flavoring agents such as 1-menthol are often used to provide an instant burst of flavor. However, at concentrations effective to provide an instant burst of flavor, 1-menthol or mint flavorings can also exhibit a bitter, astringent, burning taste (hereinafter "offensive taste"). the

This off-putting taste is especially strong in sugar-free gum and other confections. In sugar-coated confectionery, including chewing gum, the sugar masks the unpleasant taste of many 1-menthol and mint flavors (although high levels of 1-menthol and mint flavors still have a nasty taste). Even so, recent efforts to produce sugar-free coated chewing gum and other confectionary products have re-emphasized the difficulty of providing an initial burst of taste while avoiding the off-flavors associated with traditional flavorings. the

Methods of coating with xylitol are described in US Patent 4,105,801; US Patent 4,127,677; US Patent 4,681,766; US Patent 4,786,511; and US Patent 4,828,845. the

Various patents disclose various methods of coating with sorbitol, including British Patent 2,115,672; US Patent 4,317,838 and US Patent 4,753,790. A successful sorbitol hard coat is reported in US Patent 4,423,086, especially when the sorbitol is at least 99% D-sorbitol. However, the quality of the coating has never reached that of typical xylitol coatings. the

Other coating patents that teach the use of alternative polyols in place of xylitol include: US Patent 4,840,797 which discloses a maltitol coating requiring more than 95% maltitol to obtain a good quality coating on pellet chewing gum; 5,248,508 and 4,792,453, which disclose hydrogenated isomaltulose coatings; and US Patent 5,603,970, which discloses erythritol coatings. the

Still other patents teach the partial replacement of xylitol with sorbitol, lactitol or maltitol. However, these patents cannot be applied to the same solution, but must be applied to different solutions. In other words, a solution of one polyol is applied first, followed by another solution of the other polyol. These patents include: U.S. Patent 5,270,061; U.S. Patent 5,376,389; PCT applications PCT/US93/09354 (published as WO95/08925); is WO95/07622). the

In a brochure entitled "The Evaluation of Chewing Gum—Xylitol and the Prevention of Dental Caries", published by Xyrofin in 1985, a drug containing xylose is described. Alcohol and up to 10% sorbitol to form a coating. US Patent 5,536,511 discloses a coating comprising co-crystallized xylitol and erythritol. In a different approach than sprinkling by solution, US Patent 4,146,653 discloses a molten mixture of xylitol and sorbitol used to form the coating. the

US Patent No. 5,409,715 discloses chewing gum with a coating having a variety of materials including waxes, lipids, fatty acids, fats, oils, cellulose derivatives, modified starches, dextrins, gelatin, zein, Vegetable gums, proteins, edible polymers, edible plastic films, maltodextrins, polyols, low-calorie carbohydrate fillers, shellac, and combinations thereof. the

What is needed is a coating that provides a strong flavor impact suitable for confectionery including chewing gum that does not impart the off-taste typically associated with these coatings. What is needed is to provide coated confectionery with a better cooling effect, clean, high quality flavor, while at the same time reducing or eliminating xylitol in the presently preferred sugar-free coatings. the

Summary of the invention

The present invention incorporates a combination of physiological cooling agents into confectionery including chewing gum. A preferred embodiment of the present invention provides a confectionery, especially a chewing gum, having a clean, refreshing feel imparted by a cooling flavor composition comprising a mixture of physiological cooling agents. Another preferred embodiment also contains flavoring agents, and the physiological cooling agent composition has been treated to modulate its release from the chewing gum. The result is a synergy between the physiological cooling agent and the flavoring agent, which provides a stronger flavoring effect at a low concentration of flavoring agent. Thus, whether in accordance with either or both aspects of the invention, confectionery products can be made to have a long-lasting refreshing sensation without undesired off-flavor or flavoring characteristics. The confectionery may have a strong taste impact, as well as a clean, high quality taste with a strong refreshing effect. the

In other embodiments of the present invention, the cooling flavor composition may also be used in other cosmetic or even topical products such as creams and lotions. the

In one aspect, the present invention is a confectionery comprising menthyl glutarate and one or more selected from the group consisting of 1-isolongitol, p-menthane-3,8-diol and mixtures thereof. other physiological refreshers. the

In another aspect, the present invention is a composition of cooling flavors capable of imparting a physiological cooling effect to an oral composition used therein, comprising menthyl glutarate and selected from the group consisting of 1-isolongifolate, One or more other physiological cooling agents in p-menthane-3,8-diol and mixtures thereof. the

In another aspect, the present invention is a confectionery having a coating, wherein said coating comprises a coating material, menthyl glutarate and selected from the group consisting of 1-isolongifolate, p-menthane-3,8- One or more other physiological cooling agents of diols and mixtures thereof. the

In another aspect, the present invention is a chewing gum composition comprising a) from about 5% to about 95% of a chewing gum base; b) from about 5% to about 95% of fillers and sweeteners; and c) from about 0.1% Up to about 10% flavoring agent, wherein the flavoring agent comprises menthyl glutarate and one or more selected from 1-isogalementhol, p-menthane-3,8-diol and mixtures thereof Other Physiological Refreshing Agents. the

In a preferred embodiment, the composition of physiological cooling agents is treated to obtain a modified release. Controlled release of the physiological cooling agent composition is obtained by modifying the cooling agent by encapsulation, partial encapsulation or partial coating, entrapment or absorption with water soluble or water insoluble materials. Processes for modifying the physiological cooling agents include spray drying, spray cooling, fluid bed coating, coacervation, extrusion and other coalescence and standard encapsulation techniques. The cooling agents may also be absorbed into inert or water insoluble materials. The cooling agents may also be modified in a multi-step process comprising any of the described methods. the

A preferred embodiment of the present invention provides a confectionery coating having a clean, refreshing feel in which some or all of the xylitol has been replaced by a less expensive coating material. the

Other preferred embodiments also comprise a flavoring agent, wherein the synergy between said physiological cooling agent and said flavoring agent provides a stronger flavoring effect at a lower flavoring concentration. The addition of the physiological cooling agent provides an unexpected, stronger flavoring effect to the coated confectionery, wherein the off-taste is reduced or eliminated. This is especially valuable for sugar-free confectionery where the off-flavor of the flavoring cannot be masked by sugar. the

The foregoing and other features and advantages of the present invention will become apparent from the following detailed description of preferred embodiments when considered in conjunction with the accompanying examples. Detailed description of preferred embodiments of the present invention

The present invention will be described in detail below. In the following, different aspects of the invention are defined in more detail. Each defined aspect can be mutually combined with any other single aspect or aspects unless stated otherwise. In particular, any stated preferred or advantageous feature may be combined with any other preferred or advantageous feature. the

In the context of the present invention, chewing gum refers to chewing gum, bubble gum and the like. Also, all percentages are by weight unless otherwise specified. Furthermore, although certain terms are described in the singular, it should be understood that these parameters also include the plural. For example, although chewing gum coatings are described in the singular, it should be understood that coated chewing gums generally contain multiple layers of coatings. The phrase "coating" thus refers to one or more coatings. Finally, all references cited herein are incorporated by reference in their entirety.

Chewing gum compositions tend to inhibit the release of their flavoring agents. While a slower release is desirable in most cases, some consumers do prefer an instant burst of intense flavor. One way of giving chewing gum a stronger taste effect is to add encapsulated flavoring agents to the chewing gum. For example, for a cool and refreshing taste, cooling flavors such as encapsulated 1-menthol and/or mint flavors may be added to the chewing gum. 1-Menthol/menthol compositions are disclosed in US Patent 4,724,151. the

However, the improved taste effect of adding cooling flavors to chewing gum or other confectioneries is offset by the disadvantages of bitterness, astringency, and burning sensation associated with high concentrations of these flavors. This shortcoming is especially critical for sugar-free candies and gums, where sugar can mask those unpleasant tastes. the

The inventors have found that adding a combination of physiological cooling agents or modified release of cooling agents from chewing gum provides a more pleasing flavoring effect. Thus, the inventors were able to reduce or eliminate the unpleasant taste associated with prior art chewing gums and candies with stronger flavoring effects. the

By adding a composition of physiological cooling agents to 1-menthol or mint type flavored confectionery, one skilled in the art can obtain an intensely refreshing and clean mint taste without the high Concentration of 1-menthol or peppermint flavoring. Also, the immediate release of the encapsulation of the physiological cooling agent composition complements the mint flavor to achieve the stronger effect of taste and cooling typically found in chewing gum and confectionery. This refreshing effect is similar to that of 1-menthol, but without the bitterness associated with 1-menthol. the

Another way to provide a stronger taste effect to a confectionery is to add flavoring agents to the coating of the coated confectionery. For example, for a refreshing and refreshing taste, cooling flavorings such as l-menthol and/or mint flavoring may be added to the coating of the confection. the

However, the improved taste effect of adding cooling flavors to confectionery coatings is offset by the disadvantages of bitterness, astringency, and burning sensation associated with high concentrations of these flavors. This shortcoming is especially critical for sugar-free products, since sugar can mask these unpleasant tastes. the

The addition of a mixture of physiological cooling agents to the coating provides a pleasing taste effect. Thus, even in the case of sugar-free coated products, it is possible to reduce or eliminate the off-taste associated with prior art coated confectioneries with stronger flavoring effects. the

By adding a mixture of physiological cooling agents to 1-menthol or mint-type flavored confectionery, one skilled in the art can obtain a strong refreshing and clean mint taste without the need for coatings as described in the prior art. A higher concentration of 1-menthol or mint flavoring is required. Likewise, the physiological cooling agent complements the mint flavoring to give the stronger effect of taste and refreshing typically found in confectionary. This cooling effect is similar to that of 1-menthol, but without the bitterness associated with 1-menthol. the

The coated chewing gum of the present invention can be made from a variety of chewing gum compositions. The chewing gum is prepared according to conventional chewing gum, forming pellets or balls. The pellets/balls are then coated using methods known in the art, such as the conventional pouring method used to coat chewing gum. The coatings are usually applied in multiple layers, where the composition of one layer is not necessarily the same as that of the other layers. the

The coating in a preferred embodiment of the invention comprises a mixture of at least one coating material and a physiological cooling agent. May also contain other ingredients such as flavoring agents, artificial sweeteners and dispersing agents, coloring agents, film formers and binders. the

Coating materials make up the majority of chewing gum coatings. Examples of coating materials include sugars such as sucrose, mannose, glucose, and glucose syrup; sugars such as maltitol, lactitol, xylitol, mannitol, erythritol, sorbitol, hydrogenated isomaltulose, and hydrogenated starch hydrolyzed The polyols of the product; and combinations thereof.

Xylitol coatings are becoming more common for sugar-free gums because xylitol has nearly the same sweetness level as sugar and cooling power due to its endothermic solvation. With such sweetness, xylitol masks the harsh taste of stronger flavorings such as l-menthol and mint flavorings. At the same time, its refreshing effect complements that of refreshing flavorings. Thus, xylitol provides a pure, high-quality refreshing effect. Its synergistic cooling effect with xylitol can be noticed when used with physiological cooling agents. However, due to its higher cost, there have been many attempts to replace xylitol in the coating with a cheaper ingredient such as another polyol. the

One problem with using polyols instead of xylitol is that they are usually not as sweet as xylitol or sugar. In the presence of high levels of flavoring agents, polyol substitutes generally provide a bitterer, less desirable tasting coated product. To some extent, high-intensity sweeteners can be used to counteract the bitterness, but also have some unacceptable taste. Also, certain polyols themselves can cause bitterness. the

Physiological cooling agents include any type of physiological cooling agents. However, in the context of the present invention, the term "physiological cooling agent" does not include conventional flavor derivatives such as 1-menthol or menthone. Preferred physiological cooling agents do not have a perceivable taste of their own, but simply provide a cooling effect. the

Since the physiological cooling agents do not have their own perceivable taste, they can be used with other types of flavoring agents to provide new and unique benefits, such as breath freshening. Most breath-promoting confectioneries are mint flavored preparations that contain moderate to high levels of 1-menthol. 1-Menthol is a constituent of peppermint oil, which has refreshing properties and can provide consumers with a refreshing feeling in the mouth. the

Paradoxically, certain cinnamon-flavored products have also been marketed for their breath-freshening properties, based on the physiological heating of cinnamaldehyde and other flavor components. In some cases, 1-menthol or peppermint oil is added to cinnamon-flavored preparations to provide a cooling sensation that mixes with the heating sensation and enhances breath freshening. While some consumers prefer the presence of mint in cinnamon confections, others describe the taste as "cloudy," "disgusting," and "messy," preferring the "pure" cinnamon flavor . the

Many consumers do not like the addition of mint flavors to cinnamon-flavored candies and chewing gums, but prefer the addition of non-menthol, physiological cooling agents to such products. Furthermore, the preferred products of the present invention have greatly enhanced breath freshening properties compared to cinnamon flavored confectionery without physiological cooling agents. the

The confectionery of the present invention may be any new or existing type of product in this category. Specifically, hard candies, hard or soft sprinkles, chewable confectionaries and powdered sugars are covered. Chewing gum is a preferred embodiment. the

Although there are already references disclosing the use of physiological cooling agents in chewing gum and other confectioneries, unique combinations and controlled release are still new areas of interest. Because flavors impart distinct and unique sensations when used in chewing gum, certain combinations of physiological cooling agents can provide unique benefits and can be combined with multiple types of flavors or with multiple encapsulated Combined with coating methods to achieve controlled release. the

Several US and foreign documents disclose specific compounds and families of compounds as physiological cooling agents. Some of them also disclose the use of physiological cooling agents in chewing gum. These documents include:

U.S. Patent 5,451,404 (ketal (1-menthol or carboxamide) in combination with another cooling agent);

U.S. Patent 5,372,824 (physiological cooling agents and reduced 1-menthol);

US Patent 5,348,750 (menthone ketal);

氧基丙烷-1，2-二醇)； US Patent 5,326,574 (spray dried 3-1-

oxypropane-1,2-diol);

US Patent 5,266,592 (menthone glycerin ketal);

US Patent 5,165,943 (Cyclodextrin Complexes with Physiological Cooling Agents);

U.S. Patent 5,009,893 (p-menthane carboxamide physiological cooling agent with 1-menthol for reducing bitterness);

氧基丙烷-1，2-二醇)； US Patent 4,459,425 (3-1-

oxypropane-1,2-diol);

US Patent 4,296,093 (Substituted Cyclohexanamides);

U.S. Patents 4,248,859 and 4,318,900 (alkyl-substituted fatty carboxylic acids, esters or amides);

U.S. Patents 4,157,384 and 4,029,759 (various 3-substituted p-menthanes);

US Patent 4,081,480 (α-oxy-mercaptan);

U.S. Patent 4,070,449 (sulfoxides and sulfones);

U.S. Patents 4,060,091; 4,190,643 and 4,136,163 (substituted p-menthane-3-carboxamides);

U.S. Patents 4,153,679; 4,296,255 and 4,230,688 (aliphatic carboxamides);

U.S. Patent 4,034,109 (aliphatic sulfonamides and sulfenamides);

US Patent 4,033,994 (p-menthane-3-carboxylate);

U.S. Patents 3,793,446 and 3,644,613 (ketoesters of menthol);

US Patent 3,720,762 (spilanthol containing 1-menthol or peppermint oil);

Canadian Patent 2,101,790 (carbonic acid with free polar groups);

German patent 2,608,226 (menthyl lactate);

German patent 2,433,165 (menthyl N-acetylglycinate);

French patent 2,577,922 (L-menthyl-3-hydroxybutyrate);

Japanese patent 94/065023 (1-2-isopropenyl-5-methylcyclohexanol, also known as 1-isolongifolin);

British Patent 1,502,680 (bicyclic acids, esters, amides and substituted menthols);

UK Patent 1,476,351 (cyclic and aliphatic amides, ureas and sulfonamides);

British Patent 1,442,998 (trialkyl-substituted cyclohexanecarboxamide);

UK Patents 1,421,744 and 1,421,743 (new amides);

British patent 1,411,786 (cyclohexaneamide);

British Patent 1,404,596 (aliphatic secondary and tertiary alkanols);

PCT publication WO97/07771 (menthyl succinate and carboxamide);

PCT publication WO96/28133 (refreshing agent composition for cosmetics);

PCT publication WO96/17524 (refreshing compositions containing N-substituted p-menthane carboxamides and 1-menthol);

PCT publication WO94/010117 (cyclohexanol derivatives); and

US Patent 3,639,569 (physiological cooling agents). the

Specific examples of physiological cooling agents include:

1) Substituted p-menthane, substituted p-menthane-carboxamide (eg, N-ethyl-p-menthane-3-carboxamide (FEMA3455)), aliphatic carboxamide, substituted cyclohexane amides, substituted cyclohexanecarboxamides, substituted ureas and sulfonamides, and substituted menthols (all from Wilkinson Sword);

2) hydroxymethyl and hydroxyethyl derivatives of p-menthane (from Lever Bros.);

3) menthyl succinate;

4) 2-mercapto-cyclo-decanone (from International Flavors and Fragrances);

5) 1-2-isopropenyl-5-methylcyclohexanol (from Hisamitsu Pharmaceuticals, hereafter referred to as "1-isolongitol," FEMA2962);

6) Hydroxycarboxylic acids with 2-6 carbon atoms;

7) Menthone glycerin ketal (FEMA3807, trade name FRESCOLAT ^TM type MGA);

8) Menthyl propylene glycol carbonate (FEMA 3806);

9) Menthol glycol carbonate (FEMA 3805);

10) 3-1- Oxypropane-1,2-diol (from Takasago, FEMA3784, (hereinafter referred to as "TCA"));

11) Menthyl lactate; (from Haarman & Reimer, FEMA3748, trade name FRESCOLAT ^TM type ML); and

12) Menthyl glutarate (Menthyl glutarate as used herein comprises menthyl mono-1-glutarate and a mixture of menthyl mono-1-glutarate with common impurities such as menthyl dipalate ). the

The combination of menthyl glutarate and one or more other physiological cooling agents selected from 1-isolongitol, p-menthane-3,8-diol and mixtures thereof is the refreshing composition of the present invention provides the basis. Although any of the above-disclosed physiological cooling agents may be used in the composition of physiological cooling agents, the following are preferably used:

1) N-substituted p-menthane carboxamides;

2) Aliphatic carboxamides (AC), such as those disclosed in U.S. Patents 4,296,255; 4,230,688; and 4,153,679; all of which are assigned to WilkinsonSword;

3) Menthone glycerol ketal (MGK);

4) Menthyl lactate (ML);

5) Menthyl succinate (MS); and

6) 3-1- Oxypropane-1,2-diol (TCA).

1-menthol may also be included in the composition. the

In the present invention we have surprisingly found that a mixture of menthyl glutarate and 1-isoeleganthol forms a cooling combination similar in nature to the high quality single cooling agent WS-23 when used in chewing gum things. A mixture of menthyl glutarate and p-menthane-3,8-diol (hereinafter referred to as "menthanediol") can also provide the same effect. Also unexpected was the discovery that a triphasic mixture of 1-isolongifolate, menthyl glutarate and menthanediol gave

High quality refreshing effect similar to WS-23. the

In chewing gum, only the combination of 1-isolongifolate and menthyl glutarate gave a better refreshing mixture. The ratio of these two compounds may be between about 3:1 to about 1:3, and preferably about 1:1. In confectionery it is preferred to use all three of these physiological cooling agents. In this case, the ratio of menthyl glutarate to the combination of 1-isolongitol and menthanediol is between about 20:3 and about 60:3, preferably about 40:3. In confectionery using all three of these physiological cooling agents, the preferred ratio of 1-isolongitol to menthanediol is between about 1:3 to about 3:1, and most preferably about 1:1 . the

The concentration of the physiological cooling agent depends on the strength of the physiological cooling agent and the desired cooling effect. Generally, cooling agents are used at a concentration of between about 0.001% and about 2% by weight of the chewing gum. Preferred concentrations of cooling agents are between about 0.01% and about 1.0%, more preferably between about 0.02% and about 0.5% in chewing gum, and between about 0.001% and about 0.1% in candies. Preferably at least 5 ppm physiological cooling agents are included in the confectionery. Preferably at least 25 ppm of physiological cooling agent and at least 5 ppm of 1-isolongifolate are included in the chewing gum preparation. the

The present invention relates to two or three physiological cooling agents, in particular 1-isolongitol, menthyl glutarate and menthanediol, which can be added to flavorings for the preparation of chewing gums or candies. In another aspect, the flavoring and cooling agents may be added independently at any stage during the manufacture of the chewing gum or confectionery product. the

These flavors include any flavor known in the art to be of food acceptable quality, such as essential oils, synthetic flavors or mixtures thereof. These flavorings include, but are not limited to, oils obtained from plants and fruits such as lemon oil, fruit essence, peppermint oil, spearmint oil, eucalyptus and other mint oils, clove oil, oil of wintergreen, cinnamaldehyde, anise, and the like. Strong flavorings, such as menthol flavorings are also encompassed by the present invention. Preferred flavorings include cooling flavors such as peppermint, eucalyptus, l-menthol, wintergreen and fruit-mint; non-cooling flavors such as spearmint and cinnamon, and combinations thereof. the

Artificial flavoring ingredients are also included in the present invention. Those skilled in the art will appreciate that natural and artificial flavoring agents may be combined in any combination that is perceptually acceptable. All such flavorings and combinations are included in the present invention. the

The amount of flavoring agent added to the chewing gum formulation is such that it contains from about 0.1% to about 10% flavoring agent, preferably from about 0.2% to about 3.0% flavoring agent, and most preferably from about 0.5% to about 2% flavoring agent agent. The level of flavoring used in the candy was slightly reduced. the

For 1-menthol flavored candies and chewing gums, the combination of physiological cooling agents described above allows for a reduction in the overall concentration of 1-menthol. However, 1-menthol cannot be completely removed because 1-menthol has a distinctly recognizable taste and refreshing sensation. Therefore, in the case of flavoring with 1-menthol, physiological cooling agents can only increase the degree of refreshing while reducing the bitterness of 1-menthol. the

Accordingly, the present invention also relates to the provision of novel cooling flavor compositions which contribute to a long-lasting cooling sensation. In non-mint products, the cooling flavor compositions described above can be substituted for peppermint oil, resulting in enhanced cooling without the development of harsh or undesirable flavor profiles. Of course, they can also be used in the preparation of peppermint oil flavoring. the

Because the cooling flavor compositions of the present invention do not introduce undesired mint flavor into non-mint products, these compositions can be used to add cooling to fruit and other flavors. the

Due to their low solubility in water, physiological cooling agents are usually released slowly from the gum during the early stages of chewing the gum. However, some consumers prefer TCA which is moderately fast release, others prefer WS-3, WS-23 which is moderately slow release, while others prefer menthone glycerol ketal, menthyl lactate and succinate The release of menthyl acid is very slow. the

Certain combinations of the above cooling agents not only have a synergistic effect, but also provide medium release and slower release to give flavor effect and flavor continuation. Physical modification of the physiological cooling agent by encapsulation using other substrates will also modify the release of the physiological cooling agent in chewing gum by improving its solubility or dissolution rate. Any standard technique capable of partial or complete encapsulation of the combination of physiological cooling agents may be used. These techniques include, but are not limited to, spray drying, spray cooling, fluid bed coating and coacervation. These encapsulation techniques capable of achieving partial encapsulation or complete encapsulation can be used alone or in any combination in a single step or multiple steps. Typically, the modified release of the physiological cooling agent is obtained in multiple steps such as spray drying of the combined physiological cooling agent, followed by fluid bed coating of the resulting powder. the

Four methods that can be used to achieve modified release of physiological cooling agents are: (1) encapsulation by spray drying, fluid bed coating, spray cooling and coacervation to achieve complete or partial encapsulation; (2) coagulation to achieve partial encapsulation. (3) fixation or absorption can also achieve partial encapsulation; and (4) pinching by extrusion. Combinations of these four methods in any available manner to physically separate the physiological cooling agent, improve its solubility, or improve the release of the physiological cooling agent are encompassed by the present invention. the

The cooling flavor compositions and encapsulated, agglomerated or absorbed physiological cooling agents described above may be conveniently incorporated into chewing gum compositions. Typically, the physiological cooling agents may be added to the chewing gum either in the form of a cooling modulator composition or as part of a modified release combination of physiological cooling agents. However, both aspects of the invention can be used in the same chewing gum formulation and the cooling flavor composition itself or its individual ingredients can be treated to obtain modified release. The remaining ingredients of the chewing gum are not critical to the invention. In other words, the cooling flavor composition and/or coated granules of physiological cooling agents can be included in conventional chewing gum formulations in a conventional manner. Cooling flavor compositions and coated physiological cooling agents can be used in conventional chewing gum or bubble gum. the

In other embodiments of the invention, especially coatings of chewing gum, the concentration of physiological cooling agent depends on the strength of the physiological cooling agent and the desired cooling effect. Generally, cooling agents are used at a concentration of between about 0.001% and about 1% by weight of the coating. Preferred cooling agent concentrations are between about 0.01% and about 0.5%, more preferably between about 0.02% and about 0.2%. Use lower levels of cooling agents in confectionery. the

The present invention also includes one or more flavoring agents which may be added to the syrup to prepare the coating, or applied to the gum center while the syrup coating is drying, or after the coating has dried. In addition, flavorings may be applied anywhere within the coating sequence, eg, in the 3rd, 12th, 18th, etc. coatings. the

These flavorings include any flavoring of food acceptable quality, including those described above for use in chewing gum. The flavoring agent is added to the coating syrup in such an amount that the coating contains from about 0.2% to about 1.2% flavoring agent, and preferably from about 0.7% to about 1.0% flavoring agent. the

For 1-menthol flavored coatings, the concentrations of the physiological cooling agents described above provide a reduction in the overall concentration of 1-menthol. However, 1-menthol cannot be completely removed because 1-menthol has a distinctly recognizable taste and refreshing sensation. Therefore, in the case of 1-menthol flavoring, the physiological cooling agent can only enhance the cooling effect while reducing the bitterness of 1-menthol. the

Artificial sweeteners used in coatings include, but are not limited to, synthetic substances, saccharin, thaumatin, alitame, saccharin salts, sucralose and acesulfame potassium. The amount of artificial sweetener added to the coating syrup is such that the coating contains from about 0.05% to about 0.3%, and preferably from about 0.10% to about 0.15% artificial sweetener. the

Dispersing agents are often added to syrup coatings for whitening and viscosity-reducing purposes. Dispersants of the present invention that may be used in coating syrups include titanium dioxide, talc, or any other anti-sticking compound. Titanium dioxide is the preferred dispersant of the present invention. The amount of dispersant added to the coating syrup is such that the coating contains from about 0.1% to about 1.0%, preferably from about 0.3% to about 0.6% dispersant. the

Colorants are preferably added directly to the syrup in the form of dyes or lakes. The colorant contained in the present invention includes food-grade dyes. Film formers preferably added to the syrup include methyl cellulose, gelatin, hydroxypropyl cellulose, ethyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose and the like and combinations thereof. Binders can be added as an initial coating on the gum center, or added directly to the syrup. Binders for inclusion in the present invention include gum arabic, alginates, cellulosic materials, vegetable gums, and the like. the

Conventional pouring processes typically use sucrose as a coating material, but recent technological developments in pouring allow the use of other carbohydrate materials instead of sucrose. These ingredients include, but are not limited to, glucose, maltose, erythritol, xylitol, hydrogenated isomaltulose, maltitol and other novel polyols or combinations thereof. the

Coating materials that can be mixed with the pouring modifier include, but are not limited to, gum arabic, maltodextrin, corn syrup, gelatin, cellulosic materials such as carboxymethylcellulose or hydroxymethylcellulose, starch or modified starches, vegetable gums such as alginates, locust bean gum, guar gum, and tragacanth, insoluble carbonates such as calcium or magnesium carbonate, and talc. Anti-sticking agents can also be added as pour modifiers which allow the use of various carbohydrates as well as sugar alcohols in the development of new poured or coated chewing gum products. the

The chewing gum centers of the present invention can be obtained according to the conventional manner outlined below. These centers may contain combinations of the physiological cooling agents mentioned above. the

In general, a chewing gum center composition or other chewing gum composition typically contains a substantially anhydrous and water-insoluble chewable gum base portion, a water-soluble filler portion, and generally water-insoluble flavoring agents. With the prolongation of chewing time, the water-soluble part and the flavor part gradually dissipated. The gum base portion remains in the mouth throughout the chewing process. the

Insoluble gum bases typically contain elastomers, elastomer solvents, plasticizers, waxes, emulsifiers and inorganic fillers. Plastic polymers such as polyvinyl acetate are also often included, sometimes as plasticizers. Other plastic polymers that can be used include polyvinyl laurate, polyvinyl alcohol and polyvinylpyrrolidone. the

Elastomers include polyisobutylene, butene rubber, (isobutylene isopropylene copolymer) and styrene butadiene rubber, as well as natural latex such as gum. Elastomer solvents typically include resins such as terpene resins. Plasticizers, sometimes called softeners, are usually fats and oils, including tallow, hydrogenated and partially hydrogenated vegetable oils, and cocoa butter. Commonly used waxes include paraffins, microcrystalline and natural waxes such as beeswax and carnauba. Microcrystalline waxes, especially those with a higher degree of crystallinity, can be considered as thickeners or texture modifiers. the

According to a preferred embodiment of the present invention, the insoluble gum base comprises from about 5% to about 95% by weight of the chewing gum. More preferably, the insoluble gum base comprises from about 10% to about 50% by weight of the chewing gum, and most preferably the insoluble gum base comprises from about 20% to about 35% by weight of the chewing gum.

Gum bases also typically include filler ingredients. Filler ingredients may include calcium carbonate, magnesium carbonate, talc, dicalcium phosphate, and the like. Fillers may comprise from about 5% to about 60% by weight of the gum base. Preferably, fillers may comprise from about 5% to about 50% by weight of the gum base. the

Gum bases also typically contain softeners including glyceryl monostearate and glyceryl triacetate. The gum base may also contain optional ingredients such as antioxidants, colors and emulsifiers. The present invention encompasses the use of any commercially acceptable gum base. the

The water soluble portion of the chewing gum may also contain softeners, sweeteners, flavoring agents, physiological cooling agents, and combinations thereof. Sweeteners typically act as bulking agents in chewing gum. Fillers typically comprise from about 5% to about 95% of the chewing gum composition. the

Softeners may be added to the chewing gum in order to optimize the chewability and mouthfeel of the chewing gum. Softeners, also known in the art as plasticizers or hardeners, typically constitute from about 0.5% to about 15% of the chewing gum. Emollients for inclusion in the present invention include glycerin, lecithin, and combinations thereof. Additionally, aqueous sweetener solutions such as those containing sorbitol, hydrogenated starch hydrolysates, corn syrup, and combinations thereof may also be used as softeners and binders in chewing gum. the

As noted above, the cooling flavor compositions or coated physiological cooling agents of the present invention are most likely to be used in sugar-free chewing gum formulations. However, formulations containing sugar are also within the scope of the present invention. Sugar sweeteners generally include sugary ingredients well known in the chewing gum art including, but not limited to, sucrose, glucose, maltose, dextrin, dried invert sugar, fructose, galactose, corn syrup, alone or in any combination solid etc. the

The cooling flavor compositions and physiological cooling agents of the present invention may also be used in combination with sugar-free sweeteners. In general, sugar-free sweeteners include ingredients that have a sweet-tasting profile but lack well-known sugars, which include, but are not limited to, sugar alcohols, alone or in any combination, such as sorbitol, hydrogenated isomaltulose, mannitol, Xylitol, lactitol, erythritol, hydrogenated starch hydrolyzate, maltitol, etc.

Depending on the particular sweetness release profile and desired storage stability, coated or uncoated high intensity sweeteners can be used in the chewing gum center or coating. High intensity sweeteners, preferably aspartame, can be used at levels of about 0.01% to about 3.0%. Encapsulated aspartame is a high intensity sweetener with improved stability and release characteristics compared to free aspartame. When aspartame is used, free aspartame may be added, preferably some combination of free and encapsulated aspartame. the

Optional ingredients such as colors, emulsifiers and medicaments may also be added as separate ingredients of the chewing gum composition, or as part of the gum base. the

Aqueous syrups such as corn syrup and hydrogenated corn syrup can also be used, especially if they are less wet. This can preferably be done by co-evaporating the aqueous syrup with a plasticizer such as glycerol or propylene glycol to reduce the humidity to below 10%. A preferred composition comprises hydrogenated starch hydrolyzate solids and glycerin. Such syrups and their method of preparation are discussed in detail in US Patent 4,671,967. the

The preferred method of preparing the chewing gum of the present invention is the sequential addition of the various chewing gum ingredients to any commercially available mixer known in the art. After the ingredients are thoroughly mixed, the chewing gum is poured from the blender and formed into any desired shape by rolling into sheets and cutting into bars, extruding into blocks or molding into pellets. the

Generally, the ingredients are mixed by first melting the gum base and adding it to a running mixer. Gum base can also be melted in a blender. Color or emulsifiers may also be added at this point along with the syrup and some fillers. Then add another portion of filler to the mixer. Flavoring is usually added with the bulking agent in the final portion. The cooling flavor composition of the present invention is preferably added as part of the flavor. The physiological cooling agent with coating according to the present invention can preferably be added after adding the last part of bulking agent and flavoring agent. The entire mixing process usually takes 5 to 15 minutes, but longer stirring times are sometimes required. Those skilled in the art will appreciate that many variations can be made to the procedures described above.

When a physiological cooling agent is used as part of a cooling flavor composition containing 1-menthol, the ratio of physiological cooling agent to 1-menthol is preferably between about 2:98 to about 3:2. Typically this means that from about 2% to about 60%, and more preferably from about 4% to about 25%, of the cooling composition is a mixture of the above mentioned physiological cooling agents. the

In addition to the cooling flavor compositions, if other flavors or other oral compositions are used in the chewing gum, the cooling flavor compositions listed above can be mixed with the other flavors. In addition, some of the ingredients of the cooling flavor composition can be mixed with other flavors, and some of the ingredients can be added to the chewing gum individually. However, it is preferred that any additional flavors and cooling flavor compositions be premixed prior to addition to the chewing gum. the

Once shaped, the gum center can be coated. The coating is first presented as a liquid syrup containing from about 30% to about 80% or 85% of the aforementioned coating ingredients, and from about 15% or 20% to about 70% of a solvent such as water. Typically, the coating process is done in conventional sprinkler equipment. The sugar-free chewing gum centers to be coated are placed into the sprinkling equipment to form a moving mass. the

The material or syrup that ultimately forms the coating may be applied or distributed over the chewing gum center tablet. Flavoring agents may be added before, during and after applying the syrup to the gum center. Once the coating dries to form a hard surface, more syrup can be added to create multiple coats or multiple coats. the

The temperature at which the syrup is added to the gum center pieces during the pouring ranges from about 100F° to about 240F°. Preferably, the temperature of the syrup is from about 140F° to about 200F°. Most preferably, the temperature of the syrup should be kept constant throughout the process in order to prevent crystallization of polyols in the syrup. The syrup may be mixed with, sprayed on, poured on or added to the gum center by any means known in the art. the

In other embodiments, a powder coating may be added after the liquid coating process to form a soft coating. Powder coatings may include natural carbohydrate gum hydrolysates, maltodextrin, gelatin, cellulose derivatives, starches, modified starches, sugars, sugar alcohols, natural carbohydrate gums and fillers such as talc and calcium carbonate. the

Each ingredient that coats the gum center may be applied in one or more layers. In general, multiple coats can be obtained by applying a single coat, allowing the coat to dry, and then repeating the process. The amount of solids added in each coating step depends primarily on the concentration of the coating syrup. Any number of coatings may be applied to the chewing gum center tablet. Preferably, no more than about 75 coatings are applied to the gum center. More preferably, less than about 60 coatings are applied and most preferably about 30 to about 60 coatings are applied. In any event, the present invention involves applying a sufficient amount of syrup to produce a coated chewing gum product containing from about 10% to about 65% of the coating. Preferably, the final product comprises from about 20% to about 50% coating. the

Those skilled in the art will appreciate that multiple coating syrups in predetermined aliquots may be applied to the chewing gum center in order to obtain multiple coatings. However, it is anticipated that the volume of the syrup aliquots applied to the chewing gum will vary with the coating process. the

Once the syrup coating has been applied to the chewing gum center, the invention also includes drying said wet syrup in an inert medium. Preferably the drying medium comprises air. Preferably, jet dry air is contacted with the wet syrup coating at a temperature in the range of about 70F° to about 110F°. More preferably, the dry air ranges from about 80F° to about 100F°. The invention also includes drying air having a relative humidity of less than about 15%. Preferably the relative humidity of the drying air is less than about 8%. the

Drying air may be passed through or mixed with the syrup-coated gum center by any means known in the art. Preferably, for large scale production, dry air may be blown over and around the syrup-coated chewing gum centers at a flow rate of about 2800 cubic feet per minute. Lower flow rates may be used if smaller quantities of material need to be processed, or if smaller equipment is used. If the flavoring is applied after the syrup coating has dried, the invention also includes drying the flavoring with or without a drying medium. the

The table below compares the cooling intensity and bitterness intensity of various physiological cooling agents with l-menthol. A taste test method was also developed for testing the cooling agent in comparison with 1-menthol. A 0.1 g sample of the cooling agent was diluted in 10 ml of food grade ethanol and 1 ml of this solution was diluted in 100 ml of a solution containing 5% sucrose to give a 100 ppm solution. A 10 ml amount of each cooling agent solution was held in the mouth for 10 seconds and then spit out, and the cooling and bitterness were rated by the average perception of "N" testers (initial cooling test). For calibration of testers on a 1-10 scale, a 100 ppm 1-menthol solution was prepared and first evaluated by the testers. A comparative evaluation of the remaining cooling agents with 1-menthol was then performed on a scale of 1-10. One cooling agent evaluation was performed daily, with daily corrections using a fresh 1-menthol solution. the

After examining the data, the following comments were obtained:

1. The cooling agents and mixtures can be rated when the initial cooling strength is measured or extrapolated to an average strength equivalent to 100 ppm 1-menthol. The cooling agent (measured or derived) that required the lowest ppm concentration to achieve a cooling intensity of 100 ppm 1-menthol had the highest cooling rating. Lower ppm levels of each tested substance corresponded to higher refreshing intensity - a positive attribute. The data are shown in Table 1 below. the

2. Cooling agents available as individual chemical substances can be rated on a molar basis when the initial cooling strength is measured or extrapolated to an average strength equivalent to 100 ppm 1-menthol. The lowest molar concentration of cooling agent required to achieve 100 ppm 1-menthol cooling intensity (measured or derived) gave the highest cooling rating. Lower molar levels of material detected per molecule corresponded to higher cooling intensity - a distinct attribute. The data are shown in Table 1 below. the

3. The bitterness level of cooling agents and mixtures can be rated when measured or extrapolated to an average intensity equivalent to 100 ppm 1-menthol. The cooling agent with the lowest ppm concentration required to achieve 100 ppm 1-menthol bitterness intensity (measured or extrapolated) had the highest bitterness rating. Lower ppm levels of each substance tested corresponded to higher bitterness intensity - a recessive characteristic. Of note is the association between higher levels of bitterness and the cooling agents with the highest cooling activity, with the exception of WS-3 and WS-23 (higher cooling, lower bitterness). The data are shown in Table 1 below.

Table 1

Refresher or Mixture Refreshing Strength PPM Refreshing Strength Moles Bitter PPM WS-30 63PPM 2.44X10-4M 30PPM WS-3 65PPM 3.08X10-4M 330PPM 1-Isolongifolin 87PPM 5.65X10-4M 81PPM Menthyl Lactate 95PPM 4.17X10-4M 78PPM 1-menthol 100PPM 6.41X10-4M 100PPM Menthone Glycerin Ketal 175PPM 7.87X10-4M 140PPM TCA 185PPM 8.04X10-4M 160PPM WS-23 200PPM 1.17X10-3M 320PPM Menthol Glycol Carbonate 250PPM 1.02X10-3M 155PPM WS-14 300PPM 1.26X10-3M 400PPM Menthyl succinate 325PPM 1.27X10-3M 275PPM Menthyl Propylene Glycol Carbonate 410PPM 1.59X10-3M 90PPM Menthanediol 640PPM 3.72X10-3M 200PPM high menthol 825PPM 5.81X10-3M 250PPM Menthyl glutarate 950PPM 3.52X10-3M >500PPM

In multiple multi-ingredient tests, some synergy could be noted, with higher cooling levels detected in some cooling agent combinations associated with lower levels of bitterness in other cooling agent combinations. However, the best combination of refreshing synergistically with the lowest level of bitterness was a combination of 1) menthyl glutarate and 1-isomenthyl, and 2) menthyl glutarate, 1-isomenthyl and menthanediol. mixture. the

Based on the data in Table 1 above, about 5 times more menthyl glutarate and about half the amount of 1-isolongiferol would be required to achieve the cooling effect of WS-23. However, as shown in the following examples, approximately the same levels of menthyl glutarate and very low levels of 1-isogaleglyptol/menthonediol as WS-23 can be obtained in hard candies and chewing gums compared to WS-23 -23 similar refreshing levels.

Example:

In the following examples sugar-free candy recipes were prepared (all data below are in weight percent). :

The example formulations were prepared by first mixing hydrogenated isomaltulose, xylitol, acesulfame sweetener, and color in water at a level of about 75-80% solids. These materials are mixed at about 220F°-230F° to dissolve the hydrogenated isomaltulose, xylitol, sweetener and color in the premix tank. The mixture is then pumped into a continuous vacuum cooker and heated to 290F°-310F° to obtain a hard cooked candy bar with about 1% humidity. The final formulations shown in Table 2 are on a dry weight basis. Comparative Examples A, B, and C are control samples prepared with WS-23. the

Table 2

Example A Example 1 Example B Example 2 Example C Example 3 Hydrogenated Isomaltulose 98.91 98.91 98.90 98.80 98.921 98.921 xylitol 1.03 1.03 1.02 1.02 1.025 1.025 Acesulfame 0.05 0.05 0.05 0.05 0.050 0.050 pigment 0.01 0.01 0.13 0.13 0.004 0.004 total 100.0 100.0 100.0 100.0 100.0 100.0

The premixed cooked mass is then pumped into an in-line blender where flavor, flavor extract, aspartame sweetener, acid and calcium lactate are added to the in the premix.

table 3

Example A Example 1 Example B Example 2 Example C Example 3 premix 97.72 98.70 98.03 98.02 98.90 98.88 flavoring agent 0.41 0.43 0.29 0.30 0.59 0.615 aspartame 0.06 0.06 0.06 0.06 0.06 0.06 citric acid 1.26 1.26 1.07 1.07 0.20 0.20 malic acid 0.30 0.30 0.29 0.29 - - calcium lactate 0.10 0.10 0.10 0.10 0.10 0.10 flavoring extract 0.10 0.10 0.10 0.16 0.15 0.15 total 100.0 100.0 100.0 100.0 100.0 100.0

The acid and aspartame are dissolved in water at a solids level of about 40% to about 44% prior to addition. The pre-mixed, cooked mass is then pumped into an in-line blender where flavors, acids and sweeteners are added to create the final hard candy mass. the

The flavoring used in Examples A and 1 was lemon/lime flavoring, in Examples B and 2 was fruit/lime flavoring, and in Examples C and 3 was mint/lemon flavoring. The amounts of cooling and flavoring agents and cooling agents used in the above examples are shown in Table 4.

Table 4

After cooling to about 176F on cooling belts, the stearose pieces are blended in a batch roller mill, then sized and cut, and cooled further for packaging. the

Sensory tests on preparations A and 1, B and 2, C and 3 showed that these samples had similar cooling and flavoring properties, which was also confirmed by similar evidence in consumer testing. the

Other hard candy samples were prepared using a procedure similar to that described above with minor changes in cooling, sweetening, and flavoring agents, as shown in Tables 5-7. Table 5 shows the recipes for premixing.

table 5

Example 4 Example 5 Example 6 Hydrogenated Isomaltulose 98.915 98.803 98.922 Xylitol 1.025 1.024 1.025 Acesulfame 0.046 0.046 0.046 pigment 0.014 0.127 0.007 total 100.0 100.0 100.0

Table 6 shows the recipes for hard candies. the

Table 6

Example 4 Example 5 Example 6 premix 97.50 97.84 98.68 flavoring agent 0.44 0.30 0.61 aspartame 0.06 0.06 0.06 citric acid 1.26 1.07 0.20 malic acid 0.30 0.29

calcium lactate 0.10 0.10 0.10 flavoring extract 0.34 0.33 0.35 total 100.0 100.0 100.0

Table 7 shows the flavor and cooling compositions and their amounts. Example 4 is a lemon/lime flavor, Example 5 is a fruit/lime flavor, and Example 6 is a mint/lemon flavor.

Table 7

Sensory testing of Preparations A and 4, B and 5, and C and 6 showed a cooling and flavor profile that was closer to Examples 1-3 and had better flavor and cooling properties as rated by consumers. the

The following chewing gum examples were prepared on a laboratory scale. The same formulation was used for both comparative and inventive examples. In each example, about the same level of cooling agent blend was used in place of WS-23. The formulations used are shown in Table 8. Comparative Examples D and F are mint flavored chewing gums and Comparative Example E is a black currant flavored chewing gum.

Table 8

Example D Example E Example F Gum base 25.85 32.00 30.00 calcium carbonate - 14.90 11.00 Sorbitol 49.89 45.48 49.72 glycerin 8.24 1.50 5.50 Mannitol 5.00 - - Co-evaporated hydrogenated starch hydrolyzate/glycerol 7.95 - - flavoring agent 1.24 1.35 1.70 encapsulated sweetener 1.05 0.87 0.90 encapsulated flavoring - 1.50 -

Free APM/ACK 0.13 - 0.05 Sodium carbonate 0.25 - 0.38 sodium ascorbate - 1.40 - Lecithin 0.20 - 0.40 1-menthol 0.05 1.00 0.20 WS-23 0.15 - 0.15 total 100.0 100.0 100.0

Examples E and F are coated articles with the following coating formulations:

Table 9

Example D Example E Example F gum center - 67.50 67.50 Hydrogenated Isomaltulose - 30.41 - xylitol - - 26.08 Gum Talha - 0.80 2.70 calcium carbonate - - 3.20 Titanium dioxide - 0.33 0.30 flavoring agent - 0.28 0.13 sweetener - 0.17 - wax and talc - 0.11 0.09 1-menthol - 0.36 - WS-23 - 0.018 - pigment - 0.022 - total - 100.0 100.0

In Example 7 of the present invention, 1500ppm WS-23 in Comparative Example D was replaced with 667ppm menthyl glutarate and 763ppm 1-isolongifolin. In Example 8 of the present invention, 180ppm WS-23 in the coating of Comparative Example E was replaced with 71ppm menthyl glutarate and 106ppm 1-isolongitol. In Example 9 of the present invention, 1500 ppm of WS-23 in Comparative Example F was replaced with 558 ppm of menthyl glutarate and 881 ppm of 1-isolongitol. the

Laboratory level evaluation of these inventive examples showed that the mixture of menthyl glutarate and 1-isolongitol was similar in cooling level, cooling quality and cooling duration to WS-23 compared to WS-23. the

It should be understood that the methods and compositions of the present invention encompass a variety of embodiments in addition to the few that have been illustrated and described above. The present invention can be embodied in other ways without departing from the spirit or main characteristics of the present invention. It should be understood that the addition of other components, processing steps, substances or ingredients not specifically included may adversely affect the present invention. Accordingly, the best mode of the invention excludes components, process steps, substances or ingredients other than those listed above or used in the present invention. However, the described embodiments are, in all respects considered, only illustrative and not restrictive, and the scope of the invention is therefore defined by the appended claims rather than by the foregoing description. All changes within the methods and ranges equivalent to the claims are included in the scope of the present invention.

Claims (26)

1. the confectionery that comprise physilogical cooling agents is characterized in that described physilogical cooling agents by the glutaric acid menthyl ester and be selected from the different pulegol of 1-, and are right-terpane-3, and other physilogical cooling agents of 8-glycol and composition thereof are formed.

2. the confectionery of claim 1 further comprise the 1-menthol.

3. the confectionery of claim 1, wherein said physilogical cooling agents is through the processing of encapsulation process.

4. the confectionery of claim 3, wherein said physilogical cooling agents is sealed by spray-drying process.

5. the confectionery of claim 3, wherein said physilogical cooling agents is sealed by the fluidized bed coating process.

6. the confectionery of claim 1, the processing that wherein said physilogical cooling agents wraps in extrusion process.

7. the confectionery of claim 1, wherein confectionery comprise chewing gum.

8. the confectionery of claim 1, wherein the physilogical cooling agents in the confectionery is by the glutaric acid menthyl ester, the different pulegium of 1-pure and mild right-terpane-3, the 8-glycol is formed.

9. wherein there is the glutaric acid menthyl ester in the confectionery of claim 1 and is selected from the different pulegol of 1-in the dressing on confectionery, and are right-terpane-3, other physilogical cooling agents of 8-glycol and composition thereof.

10. the confectionery of claim 9, wherein confectionery comprise chewing gum, and have the glutaric acid menthyl ester in the dressing on chewing gum and be selected from the different pulegol of 1-, and are right-terpane-3, other physilogical cooling agents of 8-glycol and composition thereof.

11. each confectionery of claim 1 to 10, wherein confectionery comprise the physilogical cooling agents of 5ppm at least.

12. claim 1 to 6,8 and 9 each confectionery, wherein confectionery comprise chewing gum products, and goods comprise the physilogical cooling agents of 25ppm at least.

13. the confectionery of claim 1, wherein confectionery comprise the different pulegol of 1-of 5ppm at least.

14. each confectionery of claim 1 to 10, wherein confectionery also comprise and are selected from the butanedioic acid menthyl ester; Menthyl lactate; 3-1-oxygen in Meng base propane-1, the 2-glycol; Right-menthane carboxamides that N-replaces; The aliphatic carboxylic acid amides; The other physilogical cooling agents of menthone glycerol ketals and composition thereof.

15. each confectionery of claim 1 to 10, wherein with glutaric acid menthyl ester and the total different pulegium of 1-pure and mild right-terpane-3, the ratio of 8-glycol is between use the different pulegol of 1-between 20: 3 to 60: 3 in confectionery, right-terpane-3, the mixture of 8-two pure and mild glutaric acid menthyl ester.

16. the confectionery of claim 15, wherein glutaric acid menthyl ester and the total different pulegium of 1-pure and mild right-terpane-3, the ratio of 8-glycol is 40: 3.

17. salubrious seasoning composition, give the composition for oral cavity physilogical cooling effect of using it, comprise physilogical cooling agents, described physilogical cooling agents comprise the glutaric acid menthyl ester and be selected from the different pulegium of 1-pure and mild right-terpane-3, other physilogical cooling agents of 8-glycol and composition thereof.

18. further comprising, the salubrious seasoning composition of claim 17, composition wherein be selected from the butanedioic acid menthyl ester; Menthyl lactate; 3-1-oxygen in Meng base propane-1, the 2-glycol; Right-menthane carboxamides that N-replaces; The aliphatic carboxylic acid amides; The other physilogical cooling agents of menthone glycerol ketals and composition thereof.

19. each salubrious seasoning composition of claim 17 to 18, wherein said other physilogical cooling agents comprise by the weight of glutaric acid menthyl ester:

A) the different pulegol of 2% to 50% 1-, and

B) right-terpane-3 of 2% to 50%, the 8-glycol.

20. the salubrious seasoning composition of claim 17 or 18 further comprises the 1-menthol.

21. the salubrious seasoning composition of claim 20, wherein the ratio of physilogical cooling agents and 1-menthol is between 2: 98 to 3: 2.

22. the salubrious seasoning composition of claim 20, wherein the ratio of physilogical cooling agents and 1-menthol is between 4: 96 to 1: 4.

23. confectionery comprise each salubrious seasoning composition of flavor enhancement and claim 17 to 19.

24. chewing gum compositions comprises:

A) 5% to 95% matrix;

B) 5% to 95% filler and sweetener; And

C) 0.1% to 10% flavor enhancement, wherein flavor enhancement comprises the glutaric acid menthyl ester and is selected from the different pulegol of 1-, and is right-terpane-3, other physilogical cooling agents of 8-glycol and composition thereof.

25. the chewing gum compositions of claim 24, wherein with the different pulegol of 3: 1 to 1: 3 1-: the ratio of glutaric acid menthyl ester is used the mixture of different pulegol of 1-and glutaric acid menthyl ester in chewing gum.

26. the chewing gum compositions of claim 24, wherein with the different pulegol of 1: 1 1-: the ratio of glutaric acid menthyl ester is used the mixture of different pulegol of 1-and glutaric acid menthyl ester in chewing gum.